(2S,3S,7S,9S)-3,7,9-Trimethyl-tridecan-2-ol | 249746-03-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,7S,9S)-3,7,9-Trimethyl-tridecan-2-ol
• CAS: 249746-03-0
• 化学式: C₁₆H₃₄O
• 分子量: 242.445
• InChiKey: CYWPZFWYONZUAG-VGWMRTNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  17.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,7S,9S)-3,7,9-Trimethyl-tridecan-2-ol 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 [(2R,3S,7S,9S)-3,7,9-trimethyltridecan-2-yl] acetate
  参考文献：
  名称：

  Sex Pheromone of the Pine Sawfly, Macrodiprion nemoralis. Stereoselective Synthesis of the Sixteen Stereoisomers of 3,7,9-Trimethyl-2-tridecyl Acetate.

  摘要：

  The sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate (5Ac) were prepared individually, each in over 99.5% stereochemical purity. The syntheses were based on the ring opening of a pure enantiomer of cis-3,4-dimethyl-gamma-butyrolactone using a pure stereoisomer of 1-lithio-2,4-dimethyloctane, the two stereogenic centres of which were introduced with high selectivity by alkylations of the amide enolates from the appropriate enantiomers of pseudoephedrine. (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecyl acetate (SRRS-5Ac) has recently been found to be the major component of the female sex pheromone of Macrodiprion nemoralis (Hymenoptera: Diprionidae). A synthetic method for the preparation of a sixteen isomer mixture of 5Ac is also presented. This mixture has been found to be biologically active in field tests.

  DOI：

  10.3891/acta.chem.scand.53-0620
• 作为产物：
  描述：

  (2S)-2-methyl-1-hexanol 在 四氢吡咯 、 咪唑 、 氢氧化钾 、 正丁基锂 、 lithium aluminium deuteride 、 硼烷四氢呋喃络合物 、 碘 、 lithium 、 一水合肼 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 、 乙腈 、 二乙二醇 为溶剂， 反应 7.42h， 生成 (2S,3S,7S,9S)-3,7,9-Trimethyl-tridecan-2-ol
  参考文献：
  名称：

  Sex Pheromone of the Pine Sawfly, Macrodiprion nemoralis. Stereoselective Synthesis of the Sixteen Stereoisomers of 3,7,9-Trimethyl-2-tridecyl Acetate.

  摘要：

  The sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate (5Ac) were prepared individually, each in over 99.5% stereochemical purity. The syntheses were based on the ring opening of a pure enantiomer of cis-3,4-dimethyl-gamma-butyrolactone using a pure stereoisomer of 1-lithio-2,4-dimethyloctane, the two stereogenic centres of which were introduced with high selectivity by alkylations of the amide enolates from the appropriate enantiomers of pseudoephedrine. (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecyl acetate (SRRS-5Ac) has recently been found to be the major component of the female sex pheromone of Macrodiprion nemoralis (Hymenoptera: Diprionidae). A synthetic method for the preparation of a sixteen isomer mixture of 5Ac is also presented. This mixture has been found to be biologically active in field tests.

  DOI：

  10.3891/acta.chem.scand.53-0620